Isopropylethanediol → 2-Isopropoxyethyl Methanesulfonate

HRID 1584503Notes

Reaction equation

HRID 1584503 reaction equation
[CH:1]([O:4][CH2:5][CH2:6][OH:7])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>ClCCl>[S:18]([O:7][CH2:6][CH2:5][O:4][CH:1]([CH3:3])[CH3:2])(=[O:20])(=[O:19])[CH3:17]

Participants

5

Reactant 3

HCID 7996IsopropylethanediolHCID 31297Methanesulfonyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 184650452-Isopropoxyethyl Methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Combine 2-isopropoxyethanol (1.0 g, 9.6 mmol), N,N-diisopropylethylamine (2.73 g, 21.12 mmol), and dichloromethane (20 mL). Cool in an ice bath. Add dropwise methanesulfonyl chloride (1.43 g, 9.6 mmol). After 2 hours, dilute the reaction mixture with dichloromethane and extract with 1M hydrochloric acid solution, a saturated solution of sodium bicarbonate, and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Distill the residue to give 2-(isopropoxy)ethyl mesylate: bp; 84° C. at 0.1 mm Hg.

Workup

  1. temperatureCool in an ice bath
  2. extractionextract with 1M hydrochloric acid solution
  3. dry with materialDry the organic layer over Na2SO4
  4. filtrationfilter
  5. customevaporate in vacuo
  6. customto give a residue
  7. distillationDistill the residue

Sources & evidence

ORD record
ord-e201e4c21747414680568c5ad563141b
Source dataset
uspto-grants-1999_08
Patent number
US05932571

Reaction notes

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